Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation

被引：17

作者：

Harcken, C ^{[1
]}

Brückner, R ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 24期

关键词：

asymmetric synthesis; elimination reactions; esters; hydroxylation; lactones;

D O I：

10.1016/S0040-4039(01)00598-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific beta -eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural alpha -alkylidene-beta -hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D-1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D-2. Competitively, dihydroxyesters 10 were formed. (C) 2001 Elsevier Science Ltd. Al rights reserved.

引用

页码：3967 / 3971

页数：5

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